Out of Pocket

Masquerade

While talking to my therapist, she remarked on how she has noticed positive changes in my attitude and that I have come a long way since I started seeing her a few months after my husband had passed. She wanted to know what methods I was using. I lied and said meditation and yoga. If you count Mark and I bending and contorting in different sexual positions once a week as yoga...

When I got out of my therapist's office I texted Mark about my latest kink. I had been seeing a lot of thirst traps of men in masks on Tik Tok (where I get most of my new kinks and fetishes) lately and wanted him to indulge me. Halloween was coming up and he planned to take me to a party. I was so excited, Halloween is my favorite holiday.

I had a hard time deciding on what costume I wanted to wear. After browsing an array of revealing outfits at Spirit Halloween, I decided on a sexy goddess outfit. A little tongue in cheek considering I live near a university dominated by fraternities and sororities. There was even a show about their rush week. I forget what it's called, but oh how I missed going to frat parties! Especially the Halloween ones. I remember the most elaborate ice luge at one of the frat houses and the president of said house hitting on me and dancing with me for most of the night. He was tall and quite handsome, but it never went anywhere. I wasn't in a sorority so I didn't really feel like I fit in, I was only there for fun and because college girls were always allowed at frat parties. I wonder how that guy is doing now. He's probably already divorced with a couple of kids.

I got ready for the party and decided to put on a beautiful white mask to match my dress because the party was mask themed. I was to go to the party alone. Mark and I were to talk and flirt with other people until we found each other and then we would take his car home because I wanted to drink a good bit and have fun. He agreed to limit himself to only a couple of drinks so he can stay alert for our scene. I liked that about Mark, he never felt the need to drink anyone under the table. He was so responsible and mature considering his age.

I ordered an uber to take me to the party. When I arrived I was offered some orange pumpkin shaped jello shots, which we delicious, and a glass of champagne. We were at a nice, big house on the rich side of town. Mark told me it was a doctor's house because he had done some work for him and so he invited Mark and a plus one to attend his annual Halloween extravaganza. When I finished my champagne, I went into the kitchen and was poured a glass of white wine. I found the hosts, introduced myself, and thanked them kindly for inviting me. The music was fun and appropriate for the theme, they played typical Halloween songs like "Phantom of the Opera" and "Monster Mash". Everyone at the party was around my age or older so I felt comfortable, but these older men and women had the means and the money to keep themselves up like I did with the insurance money I was given so it made the playing field even. The masks and costumes also worked in their favor. There were some men and women who dressed up well and looked like a vision, some who had on silly costumes, and some who wore the classics like me. Most of the men I talked to were married of course, but they were either swingers or had open marriages. I was fascinated by this and wondered if it would have helped my marriage before it was cut short on its own, but probably not. I'm open-minded, but I get a bit insecure and jealous, always have, and I have horrible abandonment issues hence the therapy. I was content with my arrangement with Mark however, and though I had talked and flirted my way through most of the house and thought several men were attractive and even gave them my number, I needed to focus on the game and figure out where Mark was and what he came as. And that's when I noticed someone tall with a Kylo Ren costume on. I got goosebumps just looking at him talking to another woman dressed as a butterfly. He eventually spotted me and made his way towards me while I finished my third glass of wine. He held out his gloved hand, I took it and without saying a word, we walked upstairs to one of the many rooms in the house stealthily.

We went into a small study room with bookshelves lining each wall. I was afraid of getting caught, but I wanted his cock in my mouth more. He ordered me to get down on my knees. He undid his pants and then shoved himself forcefully inside my mouth, hitting the back of my throat. Then he placed his gloved hands firmly on both sides of my head and proceeded to fuck my face. We had practiced for this and the alcohol had numbed some of the pain and irritation. I go above and beyond to please him because it also gets me very wet when he is enjoying himself and he knows this. He does the same for me. I felt him tense a bit, but he pulled out and then ordered me me to bend over on the nice dark cherry wood desk. Hearing his muffled voice through the mask made me feel like I was really fucking THE Kylo Ren himself. Of course underneath the costume he was not a dark haired man with mommy AND daddy issues, but a girl could dream. I think if I ever saw Adam Driver in person I'd probably get on my knees out of habit, but I digress. Mark was inside of me with one hand massaging my one of my breasts and the other working on my clit. I was so wet that it was dripping down my legs and onto the rug. The thought of this grossed me out a bit, I had no idea that I could get so turned on that I could do that, but Mark assured me after we had left the party that it was completely natural and to not be ashamed. During the drive home I was just hoping that the owners of the house would get their rug cleaned soon.

When we got to Kylo's aka Mark's house, I wanted some more drinks. We poured two glasses of red wine, sat down in his living room, and decided to actually watch Star Wars. When The Supreme Leader of the First Order appeared on the screen, I told Mark to put his Kylo helmet back on and head to the bedroom. I don't know why, but drinking always puts me in the mood for having anal sex. I guess it doesn't feel as painful when I drink so that's what I told him I wanted. He pushed my head down into the pillows after lubing up, entered my ass, and then fucked me very hard while I heard his muffled grunting and groans as I gripped his dick as much as I could. He said I was a good girl for taking Master's saber so well and then we both orgasmed loudly in unison. We took off our costumes and passed out until when we woke up in the morning and did our usual gentle morning sex routine.

When I finally left his house, I was wearing my costume again because I had forgot my overnight bag. To think I would have usually stayed home on Halloween with my two cats and handed out candy! If past me could see present me, she would either be proud or horrified, maybe a bit of both. I enjoyed the uber drive home because the driver looked me up and down, barely concentrating on the road just like the last driver before him when I was all done up before the party, but this time my hair and make up were a mess. He knows I was fucked good and I grinned while looking at my phone as if I didn't notice him staring back at me through the rearview mirror every now and then. I arrived home, showered, and laid on my bed for awhile still processing last night's events and riding the high from it until my next one.